Checkpoint Challenges Customer Photo Similar to orienteering, this physical and mental outdoor activity combines exercise and navigation into an engaging competition for active people of all skill and fitness levels.

Checkpoint Challenges


About Checkpoint Challenges

Are you passionate about hiking or walking in the park but also looking to challenge your mind?

Checkpoint Challenges offers an unmatched outdoor adventure experience. Plot your unique course between checkpoints while working on your map reading skills!

Contemporary Orienteering...

Just like in classic orienteering, each course comprises a sequence of points on a map that must be visited sequentially. Participants determine their own routes between these checkpoints and eventually return to the Start. However, rather than using a full-size paper map, your smartphone will show only the current map segment with a built-in compass, progress tracking, and hints to help you stay on track.

Select your own time and pace...

No need to wait for club meetings as our courses are available whenever you're ready. Engage in competitive action with rankings for each leg or enjoy as a recreational activity. This enriching outdoor pursuit is perfect for any active person or adventurous group.


Checkpoint Challenges Winthrop Beach

What are people saying about Checkpoint Challenges?

Customer Reviews

This is a must do for anybody who likes hiking, map reading, or orienteering!
Evan
Did this solo and really enjoyed it. Going to take some friends out next time!
Dave
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

  • GPS
  • Flat rate price
  • Team building
  • Enriching
  • Challenging
  • No reservations
  • Individuals or groups
  • Physical
  • Competition
  • Checkpoints
  • Contest
  • Compass Reading
  • Anytime
  • Active
  • Race
  • Outdoors
  • Running

Instructors have discovered that orienteering identifies with each scholastic order, from math to history to ecological attention to public approach, and it does as such in new and intriguing manners.
Core Spirit Human & Planetary Enhancement

directions
Boston Common, 16 Charles St, Boston, MA

Directory

Orienteering Event

Coolidge Corner Orienteering Event Glenwood Orienteering Event Cottage Park Orienteering Event Roxbury Crossing Orienteering Event Malden Orienteering Event Fenway Kenmore Orienteering Event Longwood Station Orienteering Event Strawberry Hill Orienteering Event Winthrop Orienteering Event East Boston Orienteering Event Medford Hillside Orienteering Event Wellington Orienteering Event Malden Centre Orienteering Event New Squantum Orienteering Event Mount Auburn Orienteering Event East Somerville Orienteering Event Fields Corner Orienteering Event Dorchester North Orienteering Event Downtown Boston Orienteering Event Cambridge Orienteering Event Allston Orienteering Event Uphams Corner Orienteering Event Point Shirley Orienteering Event Jeffries Point Orienteering Event Inner Belt Orienteering Event Mount Ida Orienteering Event Coolidge Hill Orienteering Event Beacon Hill Orienteering Event Winthrop Beach Orienteering Event Somerville Orienteering Event Chinatown Leather District Orienteering Event Forest Hills Orienteering Event Squantum Orienteering Event Back Bay Orienteering Event Quincy Market Orienteering Event Fort Winthrop Historical Orienteering Event Court Park Orienteering Event Hendersonville Orienteering Event Orient Heights Orienteering Event Waterfront Orienteering Event Reservoir Orienteering Event South Bay Orienteering Event Allston Brighton Orienteering Event Downtown Financial District Orienteering Event Chelsea Orienteering Event Jamaica Plain Orienteering Event Glendale Orienteering Event South Boston Orienteering Event West Somerville Orienteering Event Admirals Hill Orienteering Event Prospect Hill Orienteering Event Winter Hill Orienteering Event Old Cambridge Orienteering Event Brookline Orienteering Event Savin Hill Orienteering Event Spring Hill Orienteering Event Dorchester Center Orienteering Event West End Orienteering Event North Cambridge Orienteering Event East Watertown Orienteering Event Revere Orienteering Event Larchwood Orienteering Event Suffolk Downs Station Orienteering Event East Cambridge Orienteering Event Cambridgeport Orienteering Event Mission Hill Orienteering Event Dock Square Orienteering Event Beachmont Orienteering Event Edgeworth Orienteering Event Ten Hills Orienteering Event Ashmont Orienteering Event Medford Orienteering Event Mount Bowdoin Orienteering Event Sommerville Orienteering Event Faneuil Orienteering Event Bay Village Orienteering Event Meeting House Hill Orienteering Event Roxbury Orienteering Event Beaconsfield Orienteering Event City Point Orienteering Event Neponset Orienteering Event Dorchester Orienteering Event Kendall Square Orienteering Event Brighton Orienteering Event West Everett Orienteering Event Avon Hill Orienteering Event Forest Hills Orienteering Event South End Orienteering Event Dorchester South Orienteering Event Charlestown Orienteering Event Boston Orienteering Event Aberdeen Orienteering Event Brookline Village Orienteering Event North Brighton Orienteering Event North End Orienteering Event Cedar Grove Orienteering Event Everett Orienteering Event Grove Hall Orienteering Event Huron Village Orienteering Event Va Boston Healthcare System Brockton Campus Orienteering Event

Map And Compass Reading

East Watertown Map And Compass Reading Inner Belt Map And Compass Reading Forest Hills Map And Compass Reading Cottage Park Map And Compass Reading East Cambridge Map And Compass Reading East Somerville Map And Compass Reading Back Bay Map And Compass Reading Allston Brighton Map And Compass Reading South Bay Map And Compass Reading Coolidge Corner Map And Compass Reading Orient Heights Map And Compass Reading Aberdeen Map And Compass Reading Savin Hill Map And Compass Reading City Point Map And Compass Reading Revere Map And Compass Reading Beachmont Map And Compass Reading Brookline Map And Compass Reading Ten Hills Map And Compass Reading Downtown Boston Map And Compass Reading Fort Winthrop Historical Map And Compass Reading Court Park Map And Compass Reading Reservoir Map And Compass Reading Roxbury Map And Compass Reading Wellington Map And Compass Reading Everett Map And Compass Reading Winthrop Beach Map And Compass Reading New Squantum Map And Compass Reading Brookline Village Map And Compass Reading Medford Map And Compass Reading Fields Corner Map And Compass Reading Coolidge Hill Map And Compass Reading Glendale Map And Compass Reading Malden Centre Map And Compass Reading Dorchester Map And Compass Reading Downtown Financial District Map And Compass Reading Meeting House Hill Map And Compass Reading Grove Hall Map And Compass Reading South Boston Map And Compass Reading South End Map And Compass Reading Fenway Kenmore Map And Compass Reading Brighton Map And Compass Reading Winthrop Map And Compass Reading West End Map And Compass Reading Dock Square Map And Compass Reading Larchwood Map And Compass Reading Cambridge Map And Compass Reading West Somerville Map And Compass Reading Glenwood Map And Compass Reading Avon Hill Map And Compass Reading Allston Map And Compass Reading Jeffries Point Map And Compass Reading North Cambridge Map And Compass Reading Neponset Map And Compass Reading Huron Village Map And Compass Reading Charlestown Map And Compass Reading Strawberry Hill Map And Compass Reading Malden Map And Compass Reading Dorchester Center Map And Compass Reading Dorchester South Map And Compass Reading Beaconsfield Map And Compass Reading Medford Hillside Map And Compass Reading Mount Auburn Map And Compass Reading North End Map And Compass Reading Edgeworth Map And Compass Reading Suffolk Downs Station Map And Compass Reading Hendersonville Map And Compass Reading Uphams Corner Map And Compass Reading Quincy Market Map And Compass Reading Dorchester North Map And Compass Reading Waterfront Map And Compass Reading Roxbury Crossing Map And Compass Reading Bay Village Map And Compass Reading Cambridgeport Map And Compass Reading Prospect Hill Map And Compass Reading Old Cambridge Map And Compass Reading Point Shirley Map And Compass Reading Winter Hill Map And Compass Reading Somerville Map And Compass Reading Cedar Grove Map And Compass Reading Spring Hill Map And Compass Reading Mount Bowdoin Map And Compass Reading Admirals Hill Map And Compass Reading East Boston Map And Compass Reading Squantum Map And Compass Reading Mission Hill Map And Compass Reading West Everett Map And Compass Reading Longwood Station Map And Compass Reading Chinatown Leather District Map And Compass Reading Ashmont Map And Compass Reading Faneuil Map And Compass Reading Beacon Hill Map And Compass Reading Va Boston Healthcare System Brockton Campus Map And Compass Reading Mount Ida Map And Compass Reading Kendall Square Map And Compass Reading Boston Map And Compass Reading Chelsea Map And Compass Reading Forest Hills Map And Compass Reading Sommerville Map And Compass Reading Jamaica Plain Map And Compass Reading North Brighton Map And Compass Reading

Orienteering Club

West End Orienteering Club Somerville Orienteering Club Glendale Orienteering Club Meeting House Hill Orienteering Club Old Cambridge Orienteering Club Everett Orienteering Club Avon Hill Orienteering Club Admirals Hill Orienteering Club City Point Orienteering Club Wellington Orienteering Club East Cambridge Orienteering Club East Boston Orienteering Club Jeffries Point Orienteering Club Spring Hill Orienteering Club Dorchester Orienteering Club Ashmont Orienteering Club Grove Hall Orienteering Club Beacon Hill Orienteering Club Beaconsfield Orienteering Club Bay Village Orienteering Club Waterfront Orienteering Club Savin Hill Orienteering Club Fenway Kenmore Orienteering Club Downtown Financial District Orienteering Club Allston Brighton Orienteering Club Dorchester South Orienteering Club West Everett Orienteering Club Orient Heights Orienteering Club Uphams Corner Orienteering Club Prospect Hill Orienteering Club Squantum Orienteering Club Winthrop Orienteering Club Inner Belt Orienteering Club South Boston Orienteering Club Jamaica Plain Orienteering Club Point Shirley Orienteering Club Winthrop Beach Orienteering Club Aberdeen Orienteering Club Allston Orienteering Club Kendall Square Orienteering Club East Watertown Orienteering Club Mount Bowdoin Orienteering Club Forest Hills Orienteering Club Dorchester North Orienteering Club Reservoir Orienteering Club Mission Hill Orienteering Club Coolidge Hill Orienteering Club South Bay Orienteering Club Coolidge Corner Orienteering Club Glenwood Orienteering Club Fort Winthrop Historical Orienteering Club Huron Village Orienteering Club Beachmont Orienteering Club Ten Hills Orienteering Club Brookline Orienteering Club Sommerville Orienteering Club Larchwood Orienteering Club Hendersonville Orienteering Club Cedar Grove Orienteering Club Edgeworth Orienteering Club Dorchester Center Orienteering Club Cambridgeport Orienteering Club Downtown Boston Orienteering Club Brookline Village Orienteering Club Roxbury Crossing Orienteering Club Malden Orienteering Club New Squantum Orienteering Club Va Boston Healthcare System Brockton Campus Orienteering Club Court Park Orienteering Club Medford Hillside Orienteering Club Dock Square Orienteering Club South End Orienteering Club Suffolk Downs Station Orienteering Club Chinatown Leather District Orienteering Club North Brighton Orienteering Club Roxbury Orienteering Club Mount Auburn Orienteering Club Faneuil Orienteering Club North End Orienteering Club Quincy Market Orienteering Club Longwood Station Orienteering Club East Somerville Orienteering Club Forest Hills Orienteering Club Malden Centre Orienteering Club Cambridge Orienteering Club Medford Orienteering Club Neponset Orienteering Club Fields Corner Orienteering Club Mount Ida Orienteering Club Strawberry Hill Orienteering Club Revere Orienteering Club West Somerville Orienteering Club Chelsea Orienteering Club Brighton Orienteering Club Cottage Park Orienteering Club Boston Orienteering Club Charlestown Orienteering Club North Cambridge Orienteering Club Back Bay Orienteering Club Winter Hill Orienteering Club

Orienteering Meet

Charlestown Orienteering Meet Dorchester North Orienteering Meet Medford Orienteering Meet Dorchester Center Orienteering Meet Hendersonville Orienteering Meet Meeting House Hill Orienteering Meet Glenwood Orienteering Meet Va Boston Healthcare System Brockton Campus Orienteering Meet West End Orienteering Meet East Boston Orienteering Meet Inner Belt Orienteering Meet Fenway Kenmore Orienteering Meet Mission Hill Orienteering Meet Chinatown Leather District Orienteering Meet Allston Orienteering Meet South Bay Orienteering Meet Winthrop Orienteering Meet Mount Ida Orienteering Meet Fields Corner Orienteering Meet Winthrop Beach Orienteering Meet Brighton Orienteering Meet Beachmont Orienteering Meet East Cambridge Orienteering Meet Winter Hill Orienteering Meet Ashmont Orienteering Meet Malden Orienteering Meet Huron Village Orienteering Meet Aberdeen Orienteering Meet Bay Village Orienteering Meet Downtown Financial District Orienteering Meet Beaconsfield Orienteering Meet Mount Auburn Orienteering Meet Longwood Station Orienteering Meet Waterfront Orienteering Meet South Boston Orienteering Meet Cedar Grove Orienteering Meet South End Orienteering Meet Forest Hills Orienteering Meet Larchwood Orienteering Meet Admirals Hill Orienteering Meet North End Orienteering Meet City Point Orienteering Meet Coolidge Corner Orienteering Meet Kendall Square Orienteering Meet Beacon Hill Orienteering Meet Chelsea Orienteering Meet Dorchester Orienteering Meet Roxbury Orienteering Meet Somerville Orienteering Meet Point Shirley Orienteering Meet West Somerville Orienteering Meet Avon Hill Orienteering Meet Mount Bowdoin Orienteering Meet Sommerville Orienteering Meet Malden Centre Orienteering Meet New Squantum Orienteering Meet Downtown Boston Orienteering Meet Dorchester South Orienteering Meet Cambridge Orienteering Meet Prospect Hill Orienteering Meet Grove Hall Orienteering Meet Quincy Market Orienteering Meet Jeffries Point Orienteering Meet Faneuil Orienteering Meet Glendale Orienteering Meet Forest Hills Orienteering Meet North Cambridge Orienteering Meet Revere Orienteering Meet Cottage Park Orienteering Meet Dock Square Orienteering Meet Wellington Orienteering Meet Brookline Orienteering Meet Edgeworth Orienteering Meet Medford Hillside Orienteering Meet Reservoir Orienteering Meet East Watertown Orienteering Meet Everett Orienteering Meet Strawberry Hill Orienteering Meet Court Park Orienteering Meet Suffolk Downs Station Orienteering Meet North Brighton Orienteering Meet Jamaica Plain Orienteering Meet Boston Orienteering Meet Savin Hill Orienteering Meet Uphams Corner Orienteering Meet East Somerville Orienteering Meet Old Cambridge Orienteering Meet Roxbury Crossing Orienteering Meet Spring Hill Orienteering Meet Coolidge Hill Orienteering Meet Orient Heights Orienteering Meet Fort Winthrop Historical Orienteering Meet Neponset Orienteering Meet Allston Brighton Orienteering Meet Back Bay Orienteering Meet Cambridgeport Orienteering Meet Ten Hills Orienteering Meet Squantum Orienteering Meet West Everett Orienteering Meet Brookline Village Orienteering Meet

Navigation Sport

North End Navigation Sport Glendale Navigation Sport Coolidge Hill Navigation Sport Fort Winthrop Historical Navigation Sport East Boston Navigation Sport Fields Corner Navigation Sport Brookline Navigation Sport Edgeworth Navigation Sport Forest Hills Navigation Sport Winthrop Beach Navigation Sport Grove Hall Navigation Sport Allston Brighton Navigation Sport Dorchester South Navigation Sport Malden Navigation Sport Boston Navigation Sport East Somerville Navigation Sport Reservoir Navigation Sport Dorchester North Navigation Sport Dock Square Navigation Sport Glenwood Navigation Sport Jeffries Point Navigation Sport Waterfront Navigation Sport East Watertown Navigation Sport Chinatown Leather District Navigation Sport Bay Village Navigation Sport Mount Ida Navigation Sport Wellington Navigation Sport Aberdeen Navigation Sport Chelsea Navigation Sport West Somerville Navigation Sport Fenway Kenmore Navigation Sport Charlestown Navigation Sport Suffolk Downs Station Navigation Sport Ashmont Navigation Sport East Cambridge Navigation Sport Strawberry Hill Navigation Sport Somerville Navigation Sport South End Navigation Sport Brighton Navigation Sport Revere Navigation Sport Jamaica Plain Navigation Sport South Bay Navigation Sport Coolidge Corner Navigation Sport Winthrop Navigation Sport Longwood Station Navigation Sport North Brighton Navigation Sport North Cambridge Navigation Sport Avon Hill Navigation Sport Beachmont Navigation Sport Kendall Square Navigation Sport Malden Centre Navigation Sport Old Cambridge Navigation Sport Hendersonville Navigation Sport Medford Navigation Sport Cottage Park Navigation Sport Ten Hills Navigation Sport Medford Hillside Navigation Sport New Squantum Navigation Sport West Everett Navigation Sport Mount Auburn Navigation Sport Meeting House Hill Navigation Sport City Point Navigation Sport Winter Hill Navigation Sport Quincy Market Navigation Sport West End Navigation Sport Beacon Hill Navigation Sport Squantum Navigation Sport Orient Heights Navigation Sport Prospect Hill Navigation Sport Inner Belt Navigation Sport Huron Village Navigation Sport Mount Bowdoin Navigation Sport Dorchester Navigation Sport Va Boston Healthcare System Brockton Campus Navigation Sport Downtown Boston Navigation Sport Neponset Navigation Sport South Boston Navigation Sport Cambridge Navigation Sport Cedar Grove Navigation Sport Beaconsfield Navigation Sport Faneuil Navigation Sport Roxbury Navigation Sport Admirals Hill Navigation Sport Larchwood Navigation Sport Cambridgeport Navigation Sport Roxbury Crossing Navigation Sport Dorchester Center Navigation Sport Sommerville Navigation Sport Everett Navigation Sport Savin Hill Navigation Sport Brookline Village Navigation Sport Mission Hill Navigation Sport Back Bay Navigation Sport Forest Hills Navigation Sport Point Shirley Navigation Sport Spring Hill Navigation Sport Court Park Navigation Sport Downtown Financial District Navigation Sport Uphams Corner Navigation Sport Allston Navigation Sport